Skip to content

Is it normal to feel guilty about taking a break?

David Sherry
23 min read
Is it normal to feel guilty about taking a break?

If you have a 9-5 without much pressure, it might be easy for you to disconnect on weekends, seeking escape from thinking about work.

Entrepreneurs have the opposite problem, they can't disconnect, and space isn't freeing, but rather anxiety-inducing.

If you’re a founder, have raised capital, or are freelance and live and die by the next gig, you probably feel guilt around taking any time off.

This could be time off on weekends, taking time for lunch during the day, or even taking smaller breaks during the day for a walk or for lunch.

This guilt is created from perceived social pressures and societal notions of scarcity:

  • We feel social pressures – if other people around us see us take a break, they'll see us in a lesser light.
  • We feel that we’ll fall behind – if we're not constantly working, we're "losing" out.
  • We have scarcity thinking – around clients, capital, or our ability to get work in the future.

Present struggle, for a better future?

Predicated on this guilt is the notion of going through the present struggle for a better future. We tell ourselves it's for the greater good.

That, we're not workaholics... "We're just needing to capitalize on present opportunities."

The difficulty is that it's true – the present struggle now can lead to better future outcomes around the capital, work, and company size and development.

The fine line is that this is only to a point.

And hard work is only one variable.

Hard work does not correlate directly with results, leverage, and wellbeing. There are plenty of people working harder than you, with lesser results.


Hard work needs to be matched with proper decision-making, thinking, leverage, a network, and capitalizing on the right strategy.

If your hard work is missing these other ingredients, you will "work hard" in the wrong direction for diminishing results.

Seen this way, better thinking creates more leverage.

And so the real question is, what drives better thinking?

What I've observed in myself and others is that it is space (breaks from work) create better thinking.

It's why our best ideas "happen in the shower."

Every time we take a break, every time we take ourselves out of the proverbial weeds, we go from seeing from within the glass jar to integrating and synthesizing our insights outside of it.

Breaks, and time away, are not unproductive. They are a different type of productive.

They productively help you create new insights and synthesize patterns from our experience.

Taking space can help you...

  • Re-evaluating major decisions or areas you’re stuck.
  • Finding inspiration, and having new ideas.
  • Having life experiences that are meaningful to you, outside of work.

Having space away from work is one of the main ingredients that, together, create our ability to do our best work.

Newsletter Written
by David Sherry

Hire a team. Empower others. Prioritize what’s important. Get some space. Re-focus on a bigger dream. Make your (work) and business work for you.

Every week I write publish 1-3 letters on upgrading to the mindset of the more conscious, modern business owner.

    Free. Unsubscribe at any time.

    Intuitive Productivity

    If we begin to see taking some space for ourselves as a part of the process of doing our best work, we'll be more likely to allow for it and to feel less guilt

    When, how often you take breaks, and what duration you take breaks is up to you.

    I call this intuitive productivity.

    There is no standard answer, only what you are needing in the moment. Sometimes fewer breaks are better, sometimes more breaks are better. Ultimately every context demands different approaches.

    If you can follow your needs more intuitively, and ask the question: "Would I really benefit from having a break right now?" and answer it honestly, I find that you will have a sense of when breaks and "synthesizing + having new ideas" is what's needed or if instead, it's better to focus on executing and making ideas happen.

    Rather than feeling guilt, use your breaks strategically. Disconnect to allow your mind to wander, come up with new ideas, and have new experiences that can make your life and work better.

    As always, have an amazing week,

    xx David

    BurnoutPersonal Journey